Once you get over the sticker shock of hotel prices, slap down your credit card and spend a long or very long weekend in Boston. You won’t regret it. Sister and I spent 4 days in Boston last month – seven years after we first visited – and it was worth the wait. We’ve become great travel buddies in the past seven years and know what kinds of things are important to us: 2 beds in a hotel that has air conditioning, good coffee, spots for picnics, and pretty things.
Before we left we curated a long list of cafes, instagrammable sweet spots, markets, picnic spots, and attractions we may want to stop in to. I used to be OCD on vacation, needing a plan well before we left, but realized (ahem, Laura convinced me) that it’s easier to think up every single place you might want to go, know how to get there and what times the places are open, and then each morning make a plan for the day.
Want a peek into our vacation?
(btw: this is a long one)
I don’t care much for museums or galleries or fancy restaurants or aquariums or anywhere super touristy but I love pretty places. Not because if I post a picture on instagram it’ll get a lot of like but because I like pretty places. Cobblestone streets, old buildings, street art, water front parks, beautifully designed cafes, cool hotels; that’s what I want to see.
The Boston Public Library is one of my all time favourite places. You all know how much I love libraries but this is the absolute best one. Can’t wait till sister gets married so we can celebrate in that Courtyard.
I know I said I’m not one for museums but in the spirit seeing beautiful courtyards we went to the Isabella Stewart Gardner Museum. If you’re into creepy murder mystery dinner parties, this would be the place to have one.
Over three decades, Isabella Stewart Gardner traveled the world and worked with important art patrons and advisors to amass a remarkable collection of master and decorative arts. She installed her collection of works in a way to evoke intimate responses to the art, mixing paintings, furniture, textiles, and objects from different cultures and periods among well-known European paintings and sculpture.
The collection itself was meh to me but the museum is gorgeous and Isabella’s history and personal story is fascinating.
Boston Common is a perfect place to wander, have a picnic, or just sit in the grass and people watch for an hour or three.
Insider tip: the east side (east of Charles St) is so much busier, keep away from the Tadpole Playground and Frog Pond, and settle into a shady spot under a willow tree west of Charles St.
Touted as “one of the most frequently photographed street in the US” and head north through Boston Common into Beacon Hill and straight to Acorn Street. For a dreamy, crowd-free perspective go first thing on a weekday morning. We were so happy to wander around Beacon Hill without any other tourists.
While in Beacon Hill I would pass on The Paramount. It’s listed on a bunch of “best of” websites but it was just ok. (Fast service though.) Go to Tatte Bakery instead.
We were ready to skip walking around Harvard since we’d done it in 2010 and assumed not much had changed. However, one of the best cafes and ice cream parlours are near the University so we meandered after breakfast and before ice cream. We were pleasantly surprised to see the colourful chairs in Harvard Yard were still there. Everything on the grounds is stunning!
Insider tip: If you are genuinely interested in a tour try to book a private one; we passed a few tours and there are easily 50+ people with one guide. You’ll never be able to hear everything and ask all your questions.
On Mass Ave across from Harvard is Tatte Bakery; you have to go here. HAVE TO! This is one of six locations around Boston and in my opinion (based on photos I looked at online), the most beautiful. Aside from the gorgeous interior there are a ton of pastries to choose from, fresh bread in the afternoons, and brunch on holidays and weekends.
Instead of heading back into the city via the Harvard T stop walk north on Mass Ave toward the Porter Station and go to Honeycomb Creamery. We’re always on the hunt for delicious ice cream the basic looking JP Licks wasn’t going to cut it. Small batch craft ice cream is always the right choice. The cold brew coffee chip is ah-mazing!
Built in 1912, Fenway a revered Park in the baseball world; just think of the greats to walk through the gates, to play on that field. We went to a Sunday night game but ventured out to Kenmore early to get coffee and a bagel at Pavement Coffeehouse (so good!), walk around the Fenway grounds before the crowds, shop at Target (oh yeeees!), and snoop around The Verb Hotel before heading back in the evening for the game.
ps: The Isabella Stewart Gardner Museum is also in Kenmore and less than a 10-minute walk. It’s easy to stroll around the ballpark and then go the museum if you’re interested in both.
Insider tip: check out Stub Hub for game tickets. We got a great deal for Concourse covered seats (the photo there was our view). Fenway also has wifi.
The night was hot the game was draaaaaaging (I love baseball, but damn) and we needed to get to the T Station before the last train but all I wanted was to be in stands to sing Sweet Caroline in the middle of the 8th. We sang and then left; the Sox were gonna lose anyway.
Over priced hot dogs not your favourite stadium food? Make a pre-game reservation at Sweet Cheeks BBQ. It was DELICIOUS! The chopped brisket, coleslaw, and mac n’ cheese were amazing. It’s not listed on the menu but you can order biscuits individually and having one is non-negotiable. They’re huge and warm and served with honey butter and may have been the most delicious thing I’ve ever eaten.
While Pavement in Kenmore was good, George Howell Coffee on Washington (top 2 photos; one on the left taken by sis) and the aforementioned Tatte Bakery were the absolute best!
I’m no coffee aficionado but I know what I like, and the espresso at George Howell was amazing! They have a fabulous staff (our barista was so great – he recommends the BLTs) and the space is overwhelmingly beautiful. The bottom 2 photos are from Tatte Harvard. See, gorgeous, right? It was very busy but the staff are patient and kind.
Like I said, Boston hotels are crazy expensive, so our favourite way to keep other costs down is to have picnics. Boston is full of beautiful places to enjoy an outdoor meal. For lunch our first day we went to Whole Foods in Beacon Hill for sandwiches and picniced in Boston Common (beware of pesky squirrels) and a few days later went to Whole Foods again for a hot bar meal to be enjoyed at the Charles River Esplanade. Get there early, take a set on the dock and watch the sun set over the river.
Duck boat tours: you need to do one! We didn’t go this year because we had gone on our first trip. This is fun and a perfect way to see the city. DO IT!
Don’t intend to spend a lot of time at Faneuil Hall Marketplace. The area and the architecture are breathtaking (think: Old State House and tons of Cobblestone streets) but the Market is so, so touristy and everything is run-of-the-mill and overpriced. Still want to see it? Go in the morning; walk around before heading to the nearby market or water front to wander or hit it up as part of the Freedom Trail.
For great lobster rolls: can you even go to New England without eating a lobster roll? Well I can because I hate shellfish, but generally speaking, no. James Hook Co was recommended to us by locals and sis said it was great. It’s right on the wharf and the dudes are brash (because they’re fishermen not restaurateurs) but it’s authentic. Go over the bridge at Seaport Blvd and find a seat on the Harbourwalk and enjoy your supper with a view of the water. Note: they close early.
If you’re in town for a few days get a 7 day Charlie Card for the T. Travelling by subway is so easy and extremely affordable if you’re planning on doing a lot of exploring. A 7-day pass is cheaper than 10 one-way tickets and in our 4 days we rode the T more than 10 times.
Don’t take a taxi downtown from the airport. Hop on the silver line bus from your terminal – its free!
Unless you need to always be connected, don’t bother with getting a US data add-on. There’s free wifi nearly everywhere and you can download large areas in google maps that can be accessed offline. This feature is so helpful and easy to use. I loved that we were able to navigate areas and look up destinations easily without wifi.
We avoided crowds by going places early in the morning, coming back to the hotel for mid day siestas, and then venturing out in the late afternoon and evenings.
Boston Cream Pie is not pie, it’s cake! Pie haters rejoice! You should get a slice from Omni Parker House.
I booked the hotel through ebates and hotels.com – yup, the whole city is pricey but going through ebates I got nearly $50 back in rewards cash. So, that’s cool.
And no, we still haven’t had canoli in Little Italy.